Modified bodipy dye matrix

Abstract

The present disclosure is directed towards a modified BODIPY dye matrix, luminescence-based pixels, luminescence-based sub-pixels, and methods using a modified BODIPY dyes. The modified BODIPY dye matrix includes a modified BODIPY dye and a polymer matrix including a radiation absorber.

What is claimed is: 
     
         1 . A modified BODIPY dye matrix, comprising:
 a modified BODIPY dye having the structure:   
       
         
           
           
               
               
           
         
       
       where R 1 , R 2 , and R 3  are independently selected from the group of C 1 -C 30  alkyl, C 1 -C 30  alkenyl, C 1 -C 30  alkynyl, C 1 -C 30  aryl, C 1 -C 30  alkoxy, C 1 -C 30  pheoxy, C 1 -C 30  thioalkyl, C 1 -C 30  thioaryl, C 1 -C 30  C(O)OR 4 , N(R 5 )(R 6 ), C(O)N(R 5 )(R 6 ), F, Cl, Br, NO 2 , CN, acyl, carboxylate, and hydroxyl, wherein R 4 , R 5  and R 6  are independently selected from the group of hydrogen, C 1 -C 30  alkyl, and C 1 -C 30  aryl and wherein P is a polymer or oligomer selected from the group of: 
       
         
           
           
               
               
           
         
       
       where R 7  is CO 2 R 8 , and R 8  is selected from the group of methyl, ethyl, butyl, t-butyl, and hexyl; n is from 2 to 500; z is from 2 to 500; y is from 2 to 500; and p is from 1 to 30; and
 a polymer matrix including a radiation absorber; 
 wherein the modified BODIPY dye is dispersed in the polymer matrix. 
 
     
     
         2 . The modified BODIPY dye matrix of  claim 1 , wherein the radiation absorber includes an emissive polymer selected from the group of poly(9,9′-dioctylfluorene-co-benzothiadiazole), poly[2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene vinylene], polyfluorenes, substituted polyfluorenes, polycarbazoles, substituted polycarbazoles, co-polymers of fluorene and carbazole, co-polymers of fluorene and benzothiadiazole, copolymers of fluorene and phenothiazine, and mixtures thereof. 
     
     
         3 . The modified BODIPY dye matrix of  claim 1 , wherein the radiation absorber is selected from the group of BODIPY dyes, perylenes, pyromethenes, rhodamines, sulforhodamines, coumarins, aluminum quinoline complexes, porphyrins, porphins, indocyanine dyes, phenoxazine derivatives, phthalocyanine dyes, polymethyl indolium dyes, polymethine dyes, guaiazulenyl dyes, croconium dyes, polymethine indolium dyes, metal complex IR dyes, cyanine dyes, squarylium dyes, chalcogeno-pyryloarylidene dyes, indolizine dyes, pyrylium dyes, quinoid dyes, quinone dyes, azo dyes, and mixtures and derivatives thereof. 
     
     
         4 . The modified BODIPY dye matrix of  claim 1 , wherein the radiation absorber absorbs electromagnetic radiation having a wavelength of 300 nm to 800 nm. 
     
     
         5 . The modified BODIPY dye matrix of  claim 1 , wherein the modified BODIPY dye is uniformly distributed in the polymer matrix. 
     
     
         6 . The modified BODIPY dye matrix of  claim 1 , wherein the modified BODIPY dye is tuned to match an emission energy level of the radiation absorber. 
     
     
         7 . The modified BODIPY dye matrix of  claim 1 , wherein the modified BODIPY dye emits light at a wavelength from 600 nm to 800 nm corresponding to a red color, emits light at a wavelength from 500 to 600 nm corresponding to a green color, or emits light at a wavelength from 400 nm to 500 nm corresponding to a blue color. 
     
     
         8 . A luminescence-based sub-pixel, comprising:
 a light shutter with adjustable transmission;   a luminescent layer disposed below the light shutter, the luminescent layer including a modified BODIPY dye in a polymer matrix; and   a mirror disposed below the luminescent layer for reflecting light emitted from the modified BODIPY dye;   wherein the modified BODIPY dye has the structure:   
       
         
           
           
               
               
           
         
       
       where R 1 , R 2 , and R 3  are independently selected from the group of C 1 -C 30  alkyl, C 1 -C 30  alkenyl, C 1 -C 30  alkynyl, C 1 -C 30  aryl, C 1 -C 30  alkoxy, C 1 -C 30  pheoxy, C 1 -C 30  thioalkyl, C 1 -C 30  thioaryl, C 1 -C 30  C(O)OR 4 , N(R 5 )(R 6 ), C(O)N(R 5 )(R 6 ), F, Cl, Br, NO 2 , CN, acyl, carboxylate, and hydroxyl, wherein R 4 , R 5  and R 6  are independently selected from the group of hydrogen, C 1 -C 30  alkyl, and C 1 -C 30  aryl and wherein P is a polymer or oligomer selected from the group of: 
       
         
           
           
               
               
           
         
       
       where R 7  is CO 2 R 8 , and R 8  is selected from the group of methyl, ethyl, butyl, t-butyl, and hexyl; n is from 2 to 500; z is from 2 to 500; y is from 2 to 500; and p is from 1 to 30. 
     
     
         9 . The luminescence-based sub-pixel of  claim 8 , wherein the polymer matrix further includes a radiation absorber. 
     
     
         10 . The luminescence-based sub-pixel of  claim 9 , wherein radiation absorber includes an emissive polymer selected from the group of poly(9,9′-dioctylfluorene-co-benzothiadiazole), poly[2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene vinylene], polyfluorenes, substituted polyfluorenes, polycarbazoles, substituted polycarbazoles, co-polymers of fluorene and carbazole, co-polymers of fluorene and benzothiadiazole, copolymers of fluorene and phenothiazine, and mixtures thereof. 
     
     
         11 . The luminescence-based sub-pixel of  claim 9 , wherein the radiation absorber is selected from the group of BODIPY dyes, perylenes, pyromethenes, rhodamines, sulforhodamines, coumarins, aluminum quinoline complexes, porphyrins, porphins, indocyanine dyes, phenoxazine derivatives, phthalocyanine dyes, polymethyl indolium dyes, polymethine dyes, guaiazulenyl dyes, croconium dyes, polymethine indolium dyes, metal complex IR dyes, cyanine dyes, squarylium dyes, chalcogeno-pyryloarylidene dyes, indolizine dyes, pyrylium dyes, quinoid dyes, quinone dyes, azo dyes, and mixtures and derivatives thereof. 
     
     
         12 . The luminescence-based sub-pixel of  claim 8 , wherein the luminescence-based sub-pixel is part of a reflective display. 
     
     
         13 . A luminescence-based pixel comprising three luminescence-based sub-pixels of  claim 8 , wherein each luminescence-based sub-pixel corresponds to a different color of emitted light such that the luminescence-based pixel can emit light over a spectrum of 300 to 800 nm. 
     
     
         14 . A method of illuminating a display, comprising:
 dispersing a modified BODIPY dye in a polymer matrix, wherein the modified BODIPY dye has the structure:   
       
         
           
           
               
               
           
         
       
       where R 1 , R 2 , and R 3  are independently selected from the group of C 1 -C 30  alkyl, C 1 -C 30  alkenyl, C 1 -C 30  alkynyl, C 1 -C 30  aryl, C 1 -C 30  alkoxy, C 1 -C 30  pheoxy, C 1 -C 30  thioalkyl, C 1 -C 30  thioaryl, C 1 -C 30  C(O)OR 4 , N(R 5 )(R 6 ), C(O)N(R 5 )(R 6 ), F, Cl, Br, NO 2 , CN, acyl, carboxylate, and hydroxyl, wherein R 4 , R 5  and R 6  are independently selected from the group of hydrogen, C 1 -C 30  alkyl, and C 1 -C 30  aryl and wherein P is a polymer or oligomer selected from the group of: 
       
         
           
           
               
               
           
         
       
       where R 7  is CO 2 R 8 , and R 8  is selected from the group of methyl, ethyl, butyl, t-butyl, and hexyl; n is from 2 to 500; z is from 2 to 500; y is from 2 to 500; and p is from 1 to 30; and
 exposing the polymer matrix to electromagnetic radiation. 
 
     
     
         15 . The method of  claim 14 , further comprising tuning the modified BODIPY dye to match an emission energy level of a radiation absorber in the polymer matrix.